Apartment
10.0(418 Reviews)
1 Bedroom
4 Guests
Oceanfront
Parking
Pool
Ocean View
US $212/Night
7 Nights - US $1,485
Chicago Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
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Compare Holiday Rentals, Villas & Resorts in Chicago
10.0
Apartment
10.0(14 Reviews)
1 Bedroom
2 Guests
Internet
Child Friendly
US $256/Night
7 Nights - US $1,792
US $531/Night
7 Nights - US $3,717
Apartment
10.0(234 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $253/Night
7 Nights - US $1,772
US $208/Night
7 Nights - US $1,456
Condo
10.0(231 Reviews)
2 Bedrooms
9 Guests
Hot Tub- Parking
Balcony/Terrace
Kitchen
US $458/Night
7 Nights - US $3,209
Condo
10.0(217 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $294/Night
7 Nights - US $2,060
Apartment
10.0(176 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
US $430/Night
7 Nights - US $3,010
Apartment
10.0(153 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $228/Night
7 Nights - US $1,598
Luxury Holiday Rentals in Chicago
Over 8028+ Luxury Holiday Rentals in or Near Chicago
New
Apartment
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $4,976/Night
7 Nights - US $34,831
New
Apartment
5 Bedrooms
12 Guests
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
US $4,545/Night
7 Nights - US $31,814
US $4,318/Night
7 Nights - US $30,226
Bed & Breakfast
8 Bedrooms
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $4,197/Night
7 Nights - US $29,376
New
House
12 Bedrooms
24 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $4,146/Night
7 Nights - US $29,025
House
10.0(39 Reviews)
5 Bedrooms
14 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $3,749/Night
7 Nights - US $26,240
Apartment
8 Bedrooms
16 Guests
- Parking
View- Air Conditioner
- Internet
US $3,579/Night
7 Nights - US $25,053
Apartment
10.0(1 Review)
7 Bedrooms
15 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $3,565/Night
7 Nights - US $24,952
Apartment
3 Bedrooms
1 Guest
- Hot Tub
- Kitchen
- Internet
Pet Friendly
US $3,482/Night
7 Nights - US $24,371
Top-Rated Holiday Rentals with a Pool in Chicago
Over 1297+ The Best Private Villas and Holiday Rentals in Chicago with a Pool
Apartment
10.0(68 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $225/Night
7 Nights - US $1,576
House
10.0(47 Reviews)
3 Bedrooms
7 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $582/Night
7 Nights - US $4,071
Apartment
10.0(44 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $192/Night
7 Nights - US $1,342
Apartment
10.0(15 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $517/Night
7 Nights - US $3,622
Apartment
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $463/Night
7 Nights - US $3,241
Apartment
10.0(9 Reviews)
3 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $466/Night
7 Nights - US $3,261
Apartment
10.0(9 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $419/Night
7 Nights - US $2,930
Hotel
10.0(9 Reviews)
- Pool
- Kitchen
- Air Conditioner
- Internet
US $284/Night
7 Nights - US $1,987
Apartment
10.0(7 Reviews)
4 Bedrooms
9 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,627/Night
7 Nights - US $11,392
Pet-Friendly Holiday Rentals in Chicago
Over 3194+ Pet-Friendly Holiday Rentals in or Near Chicago
Apartment
10.0(103 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $344/Night
7 Nights - US $2,407
Apartment
10.0(5 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $462/Night
7 Nights - US $3,235
Bed & Breakfast
8.0(677 Reviews)
1 Bedroom
- Parking
- Internet
- Pet Friendly
Security/Safety
US $141/Night
7 Nights - US $987
Apartment
10.0(102 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $174/Night
7 Nights - US $1,219
Apartment
10.0(5 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $318/Night
7 Nights - US $2,228
Apartment
10.0(92 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $151/Night
7 Nights - US $1,057
Apartment
10.0(73 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $239/Night
7 Nights - US $1,674
Condo
10.0(64 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
Breakfast- Parking
- Ocean View
US $457/Night
7 Nights - US $3,199
Apartment
10.0(64 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $390/Night
7 Nights - US $2,729
Large Holiday Rentals and Private Villas in Chicago
Over 1042+ Large Holiday Rentals and Private Villas in or Near Chicago
New
Apartment
9.8(14 Reviews)
2 Bedrooms
10 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $577/Night
7 Nights - US $4,042
Apartment
10.0(4 Reviews)
6 Bedrooms
20 Guests
Private Beach- EV Charge Station
- Parking
- Ocean View
US $482/Night
7 Nights - US $3,371
US $857/Night
7 Nights - US $6,001
Apartment
9.6(35 Reviews)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $353/Night
7 Nights - US $2,471
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $345/Night
7 Nights - US $2,417
Apartment
9.6(18 Reviews)
2 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $206/Night
7 Nights - US $1,442
Villa
9.6(13 Reviews)
1 Bedroom
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $619/Night
7 Nights - US $4,334
Apartment
9.6(11 Reviews)
2 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $455/Night
7 Nights - US $3,186
Apartment
9.6(8 Reviews)
1 Bedroom
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $784/Night
7 Nights - US $5,486
Wheelchair Accessible Holiday Homes in Chicago
Over 3068+ Wheelchair Accessible Holiday Homes in or Near Chicago
Apartment
10.0(61 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $288/Night
7 Nights - US $2,013
Apartment
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $702/Night
7 Nights - US $4,912
Bed & Breakfast
9.8(217 Reviews)
1 Bedroom
- Breakfast
- Kitchen
- Air Conditioner
- Internet
US $305/Night
7 Nights - US $2,138
Apartment
10.0(59 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $267/Night
7 Nights - US $1,871
House
10.0(1 Review)
1 Bedroom
8 Guests
- View
- Air Conditioner
- Internet
- Pet Friendly
US $385/Night
7 Nights - US $2,692
Condo
10.0(15 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $371/Night
7 Nights - US $2,596
Apartment
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $415/Night
7 Nights - US $2,903
Apartment
10.0(11 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $677/Night
7 Nights - US $4,741
Apartment
10.0(10 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $143/Night
7 Nights - US $1,003
Chicago Private Villas and Holiday Homes Under $200
Over 3009+ Chicago Private Villas and Holiday Homes Under $200
Apartment
10.0(64 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $160/Night
7 Nights - US $1,118
House
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $82/Night
7 Nights - US $574
US $109/Night
7 Nights - US $766
Apartment
10.0(58 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $172/Night
7 Nights - US $1,201
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $185/Night
7 Nights - US $1,295
Apartment
10.0(55 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $179/Night
7 Nights - US $1,252
Apartment
10.0(52 Reviews)
1 Bedroom
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,118
Apartment
10.0(17 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $175/Night
7 Nights - US $1,226
New
Apartment
10.0(17 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $162/Night
7 Nights - US $1,133
Instantly Bookable Holiday Homes in Chicago
Over 4757+ Instantly Bookable Holiday Homes in or Near Chicago
Apartment
10.0(123 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $475/Night
7 Nights - US $3,322
Apartment
10.0(6 Reviews)
1 Bedroom
5 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $190/Night
7 Nights - US $1,330
Apartment
10.0(89 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $249/Night
7 Nights - US $1,743
Apartment
10.0(88 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $310/Night
7 Nights - US $2,168
Apartment
10.0(86 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $236/Night
7 Nights - US $1,650
House
10.0(75 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $488/Night
7 Nights - US $3,416
Condo
10.0(63 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $210/Night
7 Nights - US $1,468
Apartment
10.0(62 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $468/Night
7 Nights - US $3,279
Apartment
10.0(59 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $222/Night
7 Nights - US $1,553
Book a Last Minute Place to Stay in Chicago
About Casai's Private Villas and Holiday Rentals in Chicago
Discover more than 8037 vacation rentals available in Chicago. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chicago.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chicago, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chicago. On average, places to stay near Chicago offer 757.46 ft², with nightly prices averaging US $382.
With Casai, finding and comparing holiday rentals in Chicago is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Chicago, IL
There are 8037 Chicago, IL Holiday Rentals
- Prices for a holiday home in Chicago start at US $7
- Top rated vacation home in Chicago is 52nd Floor MagMile Penthouse Views Fireplace Pool
- Most popular short term in Chicago is Riu Plaza Chicago
- Cheapest place to stay in Chicago is Homan Square
- Most expensive holiday rental in Chicago is Spacious Luxury 6BR Suite with Jacuzzi and Pool Table
Frequently Asked Questions About Chicago?
What are the top holiday rentals in Chicago?
With numerous options available in Chicago, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chicago:
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- Remodeled, spacious and bright apartment — near Loyola, beach & subway
- 51st Floor MagMile Penthouse Views Balcony Pool
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
- 1F Chicago's Little italy Graystone nearDowntown
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
How many holiday rentals have private pools in Chicago?
Discover a selection of holiday rentals with private pools near Chicago with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Chicago are best for families?
If you're searching for a family-friendly holiday home in Chicago, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chicago:
How many Casai.nz holiday rentals are available in Chicago?
As of 2026, Casai boasts over 8037 properties listed in the Chicago area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1386 |
| The Loop Vacation Rentals in Chicago, Illinois | 620 |
| Near North Side Vacation Rentals in Chicago, Illinois | 584 |
| River North Vacation Rentals in Chicago, Illinois | 348 |
| South Loop Vacation Rentals in Chicago, Illinois | 295 |
| Near South Side Vacation Rentals in Chicago, Illinois | 277 |
| Lakeview Vacation Rentals in Chicago, Illinois | 227 |
| West Loop Vacation Rentals in Chicago, Illinois | 182 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 128 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 71 |
| Edgewater Vacation Rentals in Chicago, Illinois | 61 |
| Logan Square Vacation Rentals in Chicago, Illinois | 55 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 54 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 54 |
| O'Hare Vacation Rentals in Chicago, Illinois | 48 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 38 |
